


Five Times Ransom and Holster Use Makeshift Sex Toys (Plus One Time They Get the Real Deal)

by sadtomato



Category: Check Please! (Webcomic)
Genre: Blindfolds, Bondage, Butt Plugs, Dom/sub, Gags, Impact Play, Improvised Sex Toys, M/M, Masturbation, Porn Watching, Porn with Feelings, Ransom is a coral reef, Wax Play
Language: English
Status: Completed
Published: 2016-04-24
Updated: 2016-04-24
Packaged: 2018-06-04 06:04:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,700
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6644296
Author URL: https://archiveofourown.org/users/sadtomato/pseuds/sadtomato
Summary: <blockquote class="userstuff">
              <p>Literally exactly what it says in the title.</p>
            </blockquote>





	Five Times Ransom and Holster Use Makeshift Sex Toys (Plus One Time They Get the Real Deal)

**Author's Note:**

> Some of the things in the tags are discussed rather than performed in the story. Not sure what the tagging rules are for that sort of thing, but I took my best guess at what would be appropriate.

**One**

They’re cuddled up in the bottom bunk, watching porn on Ransom’s laptop. 

“That look fun to you, Rans?” Holster asks, his arm slung over Ransom’s shoulders. He pulls Ransom a little closer, kissing his temple. The guy on screen is blindfolded, tied to a hook in the ceiling, and his partner is teasing him. It looks _very fun_ to Ransom, who is breathing heavily and clutching Holster’s t-shirt in his fist. 

“Yeah,” he breathes. 

“We could try it, if you want,” Holster suggests. They’re still trying to figure this out--what they both want, the boundaries, what turns each other on. It became pretty obvious early on that the kinky stuff was important to Ransom--Holster spanked him before he ever sucked his cock. 

“You got a blindfold?” Ransom asks, teasing. “And something to bolt to the ceiling that will hold up my 200 pound ass?”

“Well, okay, maybe not the suspension part,” Holster says, peering up at the ceiling. “Not sure the Haus would survive. But yeah, I can get you a blindfold.”

He climbs over Ransom and moves to their closet, ducking his head in to rifle through Ransom’s side. He pulls out a red necktie and holds it up, victorious.

“No way, bro, you can’t fuck up my only tie,” he says. They’d both started the school year with a few, but each boy had lost a tie here or there (mostly abandoned in locker rooms around the northeast). They were each down to one. 

Holster frowns. “What else could we use?”

“I don’t know, man,” Ransom shrugs. “Any long, thin piece of fabric I guess.”

“So, a necktie.”

Holster snaps his fingers, smirking, and says “I’ve got it. Be right back, bro.” He disappears, thundering down the attic stairs two at a time, and Ransom pauses the porn. Holster wouldn’t care, but the top is doing some crazy shit with clothespins, and Ransom maybe wouldn’t mind if Holster learned how to do that, too.

When Holster comes back, he locks the door behind him. He’s holding a plaid necktie, one that Ransom realizes has been hanging on the doorknob of the downstairs bathroom since their last game. 

“Isn’t that Nursey’s?” he asks.

Holster shrugs before climbing over Ransom, back to his spot on the bed. “Whatever, man, it’s fair game.”

“Pretty sure that shit is like, three hundred dollars,” Ransom says, grabbing the silky tie and running it through his fingers. He flips it over and points out the label to Holster. “See, Burberry.”

“Well, Nursey shouldn’t leave his Burberry lying around the Haus if he doesn’t want people using it for kinky shit,” Holster says, as though that’s an obvious outcome. “So, where were we?” 

Ransom hits play on the video, and nuzzles back under Holster’s arm. “I think this part looks good, too.”

**Two**

“Ransom, I swear to God, I will end you,” Shitty says, winding up a towel and snapping it in the direction of Ransom’s ass. “Give me back my mini pie.”

“It’s my mini pie! You ate yours, you still have crumbs in your moustache, bro.”

Shitty doesn’t relent, chasing Ransom around the locker room, the other guys ignoring them as they get dressed for the ride home. Shitty manages to pin Ransom up against his locker--only because Jack helped him, the traitor--and Ransom relents and gives up his mini pie. Shitty scored two goals tonight, so he deserves it.

Except. Except Shitty has reached a particular peak of Shittiness and decides he isn’t done with Ransom; he reaches for the roll of neon green stick tape at the top of his bag and loosens the edge with his teeth. He wraps it around Ransom’s hands a few times, binding them together, and Ransom’s heart starts to pound. He’s done this before, had his hands tied, but only with Holster, in their bedroom--privately, safely. His body associates this feeling so strongly with _need_ (and _Holster_ ) that Ransom feels his brain start to go a little fuzzy, even though this isn’t the right time or place.

“... make sure he doesn’t steal it back, right,” Shitty is saying, talking to Jack, maybe, or Bittle, but Ransom isn’t really listening to their conversation, he’s looking for Holster. He walks in from the shower, towel slung low around his hips, and Ransom makes an involuntary, desperate noise. Shitty doesn’t seem to notice, still boasting about his mini pie victory, but Holster hears him.

Holster’s on him in a second, nudging his way between Ransom and Shitty. 

“Christ, Shitty, get off him,” he says, tugging at the tape and unwinding it from Ransom’s wrists. 

“It’s cool, bro,” Shitty says, licking the last of the pie crumbs from his fingers. “We were just fucking around.”

Ransom feels better now that Holster is close and his hands are free, but he still follows Holster to his locker and clings to his side until they’re ready to board the bus.

“You alright?” Holster asks later, when they’re settled next to each other on the bus and everyone else is distracted. 

“Yeah, it was just... weird, to feel like that, around other people,” Ransom admits.

“That stick tape hurt your wrists?” Holster asks, reaching down to trace one finger around Ransom’s left wrist. 

“No, man, that part was... I, uh, didn’t mind that at all,” Ransom admits.

Holster’s face lights up. “Good thing I stole it then, huh?” he says, opening the backpack at his feet to reveal Shitty’s bright green stick tape.

Ransom laughs. “Bro, you have your own, and so do I. Why’d you steal his?”

“Nobody touches you,” Holster says, leaning in so his lips brush Ransom’s ear. “Nobody ties you up except for me.”

Ransom shudders and squirms in his seat. It’s going to be a long ride back to Samwell.

**Three**

Holster’s been spanking him since--well, since they started all of this--and it works. It really works, it brings Ransom to his knees literally and figuratively, it breaks him down, it makes him cry and makes him come. 

It’s his favorite.

But the more they do it, the more pain he wants, and Holster’s a strong dude, but he can only hit so hard with the flat of his hand. 

They try other things -- flip-flops, which Holster deem “too silly”; belts, which don’t provide the right sensation; a hockey stick, once, when they were drunk. They knocked over a lamp that time, and laughed so hard they gave up on the spanking.

Ransom’s helping Holster with his chemistry homework when Holster figures it out. They’re at the kitchen table, and Bitty’s baking, of course. Holster sneaks a strawberry from one of the sweet-smelling bowls on the counter, and Bitty catches him before he can snatch his hand away.

“Adam Birkholtz, get your filthy hands out of my kitchen,” he snaps, smacking Holster’s upper arm with the back of a wooden spoon.

“Fuck!” Holster cries, hiding on the other side of Ransom. “What the fuck, Bittle? That really hurt.”

“Bittle justice,” Bitty says, pointing the spoon at Holster and staring him down. “My mama did it to me, and I’ll do it to every single one of you boys if you mess with my pies.”

“Yeah, yeah,” Holster says, rubbing his arm where it smarts. Ransom is staring at him, biting his bottom lip, and it takes Holster a minute to catch up. Ransom looks... interested. Holster lifts up his sleeve to show Ransom the red mark where Bitty had hit him. “Think it’ll leave a bruise, bro?” he asks quietly.

Ransom reaches out to touch the mark lightly, tracing it with a fingertip. He sighs, meeting Holster’s eyes. “Yeah, I do.”

**Four**

Ransom’s hands are tied to the bedposts, Nursey’s three hundred dollar tie covering his eyes, and he’s tense and waiting. Holster’s insisted on lighting candles before they got started, and it takes forever before he touches Ransom, smoothing his hands up over Ransom’s sides and down his muscled thighs, soothing him. 

“Gonna try something new, okay?” he whispers, digging his thumbs in just under Ransom’s hipbones. “Nothing crazy, but tell me if it isn’t working, or if you want to stop.”

“Mmm,” Ransom hums, and Holster lifts his hands from Ransom’s body. 

“Rans,” he warns.

“Yeah, okay,” Ransom answers using actual words. “I’ll tell you.”

“Awesome.” Holster’s touching him again, but this time he’s using his blunt fingernails to scratch trails down Ransom’s sides. It’s not painful--at least not in the same way the spanking is--but it’s sharp and different and makes Ransom squirm. Holster scratches at his chest, too, and his thighs and upper arms.

Holster takes his hands away and Ransom hears him fumbling around, hears a plastic-y tapping sound, and he can’t guess what it is. He doesn’t need to, because whatever it is, Holster will take care of him.

The next time Holster touches him, it’s not his bare hands--it’s something soft, wet, and _hot_. He hisses, tensing up, and Holster’s spreading the heat out over his stomach, and it’s more bearable then, almost pleasant.

“It’s wax,” Holster whispers, answering Ransom’s unspoken question. “Stole some art shit from Lardo.”

“It’s good,” Ransom says through his teeth, tensing in anticipation as he hears Holster going through his preparations again. “Oh, fuck,” he groans, when a drop of hot wax lands on his left pec. Holster smooths it out quickly with the tool that he’s using--feels like a paintbrush, if Ransom had to guess. 

Holster spreads the warm wax over his chest, his stomach, and down the tops of his thighs. Ransom relaxes into the sensations, lets his brain shut down and gives everything over to Holster.

He sighs when Holster clears his throat and says “Okay, all done with that, Rans. Still good? Ready for more?”

“Yeah,” Ransom mumbles. “More.”

**Five**

“No!” Ransom says, pulling back and away from Holster’s fingers. 

Holster sighs. “Okay, it’s okay.”

“Sorry, I didn’t mean--I didn’t mean it.” Ransom says. He reaches for Holster’s hand and pulls it back between his legs, guides his fingers back to his ass. “I didn’t mean it. I want to try.”

“Bro, you keep saying ‘no,’ and I just... I know it’s instinct, or whatever, but I can’t just keep going.” He swings his leg over Ransom’s body and kneels at his side, instead of over Ransom’s legs. His cock isn’t hard anymore, and Ransom feels like shit.

“Isn’t that,” he starts, swallowing down some panic, “Isn’t that why we have the safeword?”

“Yeah, I guess,” Holster admits, wiping the lube on his hand off on Ransom’s sheets. “I think I’m just... not ready. For that. For ignoring you when you say ‘no.’”

“It’s not that I don’t want you to,” Ransom explains. “I do, I really want to try, and I did it to myself like you asked and it feels good. I just have this like, mental block.”

“It’s alright, bro.” Holster lies down, curls into Ransom’s side, and scratches his fingers through his chest hair. “There’s no rush, okay?”

****  
The next day, Ransom’s in Lardo’s room, peeking through the shared bathroom into Chowder’s room, helping her plan a retaliatory strike. 

“Teach that little fucker to steal my wax melts,” she says. Ransom fist bumps her and hopes his blush doesn’t show. “I know for a fact Bitty made him a blueberry crumble and he’s hiding the leftovers in his room, as soon as he gets it out, we’re going to pounce.”

Chowder walks into his room as if on cue, and closes his bedroom door before immediately reaching for a foil-covered sheet pan under his bed. 

Lardo grabs Ransom’s hand and rushes into the room, shouting, and Ransom does his best to hold Chowder back while Lardo steals the crumble. But Chowder is stronger when he looks, especially when taken by surprise, and he manages to twist in Ransom’s grasp and push him down against the bed while he fends off Lardo with his feet.

It takes a few minutes of yelling (and Bitty barging in to mediate) before Lardo and Chowder agree to a truce. The whole time, Ransom is pressed to Chowder’s pillow, staring at the collection of Sharks merch on his bedside table. Specifically, staring at the clean, brand new hockey puck that looks like it could just fill Ransom’s mouth. He closes his eyes, pictures biting down on the hard rubber as Holster pushes inside him. 

He’s not sure if Holster will go for it, but he wants to try. 

**Plus One**

“Jesus Christ, Holtzy, where did you get that?” Ransom pushes the plug back down inside the black opaque bag as though someone could see, even though they’re alone in the attic.

“Borrowed Lardo’s car and drove to Boston,” Holster admits. “Didn’t want to have it delivered and risk someone else opening it.”

“Jesus,” Ransom breathes, walking away from Holster to sit on their bed. The top bunk hasn’t been used for anything but storage in weeks.

“Thought it might help,” Holster says shyly. “If you still, you know. Want to.”

Ransom had gotten over his general ass anxiety as soon as he relaxed enough to let Holster get a finger inside him--the gag had helped, but he didn’t need it anymore. It’s regularly on the menu now, Holster fingering Ransom until he comes, or playing with his ass while he blows him, but their attempts at actual dick-in-ass sex had all been failures. Ransom doesn’t know if it’s another mental block, or if he’s just that tight, but it’s always been too painful for them to get very far.

“Let me see it,” Ransom asks, reaching for the bag. Holster smiles and dumps the bag in Ransom’s lap before sitting cross legged on the bed next to him. Ransom reaches in and pulls out a piece of paper first--the receipt. “Fuck, Holtzy, this thing was fifty dollars?”

Holster shrugs. “It’s the best one. I, uh, made a spreadsheet,” he admits, and Ransom’s heart bursts with affection. “It’s worth it, if it helps. If you still want...” 

Holster’s so careful not to pressure Ransom for any of this, and Ransom fucking loves him for it. 

“Yeah, I still want,” Ransom leans over and kisses Holster once, sweetly. “Can we try it now?”

“Yeah, bro,” Holster says, taking the bag back from Ransom’s hand. “Come here, first. Kiss me.”

Ransom kneels up and swings a leg over Holster’s lap, settling on his thighs, and leans down to kiss him. He’s so goddamn lucky that he gets to do all of this with his best friend.

They make out for half an hour, losing clothes slowly, shifting positions and taking turns being on top. It’s chill, it’s normal, and it relaxes Ransom as much as it turns him on.

“Bro,” Holster says, after he’s flipped Ransom onto his back. “I’m gonna suck you off a little, okay? And finger you. Just what we’ve done already, nothing new yet. Cool?”

“Yeah, cool,” Ransom says, pushing at Holster’s shoulder. “Do it.”

“Bossy,” Holster chides, slapping Ransom’s thigh. Ransom’s dick twitches and he groans, shifting his legs open wider for Holster to fit between them.

Holster licks and sucks at his cock, giving him long, wet kisses but never really sucking, never giving Ransom enough pressure to get off. It’s good, it’s amazing, and when Holster traces a slick finger against Ransom’s hole he doesn’t flinch or shy away. He just opens for Holster, breathing out slowly, and it feels so good to let him in.

“That’s so great, Rans, fuck,” Holster says, ducking down to nibble on Ransom’s thigh and watch his finger disappear into Ransom’s body. “Look at you.”

“Another one, Holtzy, c’mon,” he asks, shifting his hips against Holster’s hand. “Thought you were gonna suck me off.”

Holster shifts his arm, and Ransom feels the tip of another finger pressing against him. “I said _a little_ , bro. Don’t want you to come yet.” He licks up the length of Ransom’s cock despite his argument, and sucks at the head until Ransom’s hips buck up.

“God, fuck,” Ransom swears, torn between pushing up into Holster’s mouth and down onto his fingers. “‘M ready, for the thing, do it, put it in,” he begs.

“You’re not ready,” Holster says, twisting his fingers. “Gonna stretch you some more, bro. I don’t want to hurt you.”

“I can take it,” Ransom argues. 

Holster frowns, pulls his fingers free from Ransom’s body, and crawls up until they’re face to face. 

“We’re not doing this because _you can take it_ ,” Holster says, touching his forehead to Ransom’s. “We’re only gonna do this if you want it. If it feels good.”

“It does feel good,” Ransom whispers. “I just don’t like, you know, not being able to...”

“To what?” Holster pushes, when Ransom is quiet for too long. 

“To give you that, to let you fuck me,” Ransom says, turning his face to the side so he doesn’t have to look into Holster’s eyes. 

“Bro,” Holster says, ducking his head and chasing the eye contact. “Justin, you give me everything. Fucking everything. This is not a big deal, okay? If we never have sex this way, if you never want anything to come near your ass again, I’m cool with that.”

“Yeah,” Ransom says, straining up to kiss Holster. “Yeah, I know, that’s what makes me want to try.”

“We’ve got time, babe. We’ll try it another time.”

“No way, bro,” Ransom says, wiggling under Holster’s weight. “We have no classes this afternoon and the Haus is fucking empty, I want to keep going.”

“You sure?” Holster asks, pressing a kiss to Ransom’s brow.

“Yeah, it was good, I want more.” Ransom frees a hand and nudges at Holster’s shoulder again, pushing him down, and Holster goes willingly.

This time he starts with two fingers, and more lube, and distracts Ransom with more attention to his dick. When he adds a third finger, twisting them together to open Ransom up even more, Ransom chants “Yes, yes, yes.”

“You want to try the plug?” Holster asks, when Ransom is squirming beneath him, fucking himself down onto Holster’s fingers. “We don’t have to--”

“Yeah, I want it, now, fuck,” Ransom begs. Holster pulls the toy out and coats it with lube, drizzling it all over the bed and Ransom’s thighs and making a mess. 

“You tell me the _second_ you want to stop,” Holster warns, rubbing the slick tip against Ransom’s ass. “Got it?”

“I’ll tell you,” Ransom promises. 

Holster pushes it in slowly, his eyes on Ransom’s face, and Ransom wishes he’d asked for his hands to be tied up for this. It’s a lot, the blunt pressure of the toy and Holster’s gaze on him, and he could use something to ground him. He twists the fingers of one hand in the bedsheets, and reaches out to grab Holster’s wrist with the other.

“Adam,” he says, voice hoarse and eyes wide. “Adam, it’s so big, fuck.”

“Hurts?” Holster asks, pausing.

“No, just... full,” Ransom says. He’s trembling, fighting against the instinct to pull away, but Holster is there rubbing his side, reassuring him.

“Gonna keep going, okay?” Holster says, nudging the toy a little deeper. “This is the widest part, right here. Touch yourself, Rans, want it to feel good.”

Ransom relaxes his hold on the bedsheets and grips his cock instead, stroking himself hard, tugging at his foreskin and focusing on that sensation instead of the unfamiliar ones. 

“So good, fuck, Rans, you did it,” Holster says, grinning as Ransom feels the pressure on his rim relax. “You alright?”

“Yeah, good,” Ransom gasps, still stroking his cock. “Might... think I’m gonna come.”

“That’s perfect, Rans, yeah,” Holster encourages him, tapping at the base of the plug and shifting it back and forth a little. “I want to fuck you with this, okay?”

“Yeah, fuck me,” Ransom says, eyes locked on Holster’s, hand flying over his cock. “Fuck me, Adam, God, yes,” he mumbles. 

Holster is gentle with the toy, just pulling it out enough to tug at Ransom’s ass before he pushes it back inside. It’s perfect, it’s everything, Ransom understands now why people do this. 

“Take it out,” he says, arching up into his fist. “Fuck me, want you instead, fuck me, fuck me,” he begs, but Holster is still playing with the toy, and his cock is aching, and before Holster can even respond, Ransom is coming, striping his chest and shouting with pleasure.

He laughs as he comes down, high on the pleasure and the _success_ of doing this right, confident now that he can take Holster’s cock just like he took the plug. 

“Adam, oh my fucking God,” he says, gasping for breath. He reaches for Holster with grabby hands, pulling him down and into the mess on his chest.

“You alright, Rans? Thought you were going to pass out for a second,” Holster asks. 

“I did it,” Ransom says, grinning into Holster’s neck.

“Yeah, bro, you did,” Holster confirms, pushing up on one arm to look down at Ransom’s face. “You were so fucking hot.”

Holster’s still hard, pressed up against his hip, and Ransom shifts against him.

“You want to fuck me? Now?” he offers. 

“Won’t last,” Holster admits, moving against him. “Want to wait until I can make it last, make you come like that on my cock.”

Holster groans in frustration when he can’t get the friction he wants grinding down against Ransom, and he sits up, kneeling between Ransom’s spread legs. He’s jerking himself fast, tight little strokes over the head of his dick, his eyes jumping from Ransom’s face to his chest to his ass. 

“I can’t wait,” Ransom says, dragging his fingers through the mess on his chest. “Can’t wait for you to fuck me, Adam.”

Holster comes like it was punched out of him, hunching over and spilling over Ransom’s stomach and his softening cock, bracing himself with one hand on Ransom’s chest. 

Holster falls to Ransom’s side, laughing just like Ransom had, and Ransom nudges him with his shoulder. 

“That was ‘swawesome, bro.” 

“Fucking a,” Holster agrees. “Best fifty dollars I’ve ever spent.”


End file.
